I love Oblivion. Some of my greatest gaming memories come from playing this back then. But usually ever since 1-2 years ago, every time I miss the game and decide to come back I kinda get bored pretty early and I don't know why. It might be because I'm doing the same stuff every single time.

Escape prison -> Go to Vilverin -> Join a guild that I've done before more than once and then just get bored. Come back after like 3-4 months, and repeat.

I was wondering if any of you had any interesting suggestions that would spark it up for me and make it feel like the game I enjoyed as much as before, I know it's because I haven't really changed it up or anything. Maybe just like suggestions on what I should start doing or goals or maybe certain builds, or mods you recommend because I usually play straight up vanilla. Before when I played, I remember having a powerful Breton wizard, a Khajiit Scout, and a plain old Imperial warrior. But I played those like four years ago and all the characters after them "failed".

Help meh, pleaase I miss this game so much

Perhaps you should have a set of goals that are not related to the unvarying game quests. In my last game my character was a 'collector,' with a special interest in Ayleid artifacts, so she visited every Ayleid ruin in the province (which was helped by the Phitts Artifacts mod, which provides various interesting objects to find at random); I also used the Collectible Cards mod and enjoyed finding the cards here and there. Be an explorer. I'm sure that others will have suggestions too.

Install the mod ooo, and maybe alternate start. Personally i could't play oblivion anymore because like you said every character started the exact same. OOO adds areas that are really hard for beginner characters, but has handplaced loot that is powerful if you can kill its gaurdians.

I'd also just add quest mods, have a look at the nexus, some of the top mods there are really fun. There is also a mod subforum here that would have great suggestions.

There is also a mod i like called oblivion xp, it changes how you level and makes the game feel less grindy at the beginning, which is where if find it the slowest.

This is where roleplaying comes in handy. When you're playing as a character and not as yourself you are more likely to do things that you wouldn't ordinarily do.